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Wily stage 4 in Mega Man 2 is obnoxious. The boss practically forces you to die because you're really amazing and can position Crash Bombs in just the right places you will have to die because you can't kill all the Buebeam Traps without dying, coming back with more ammo, and taking out the remaining ones. It's kind of a clever idea admittedly but not really a fun one.

The two that are most frustrating for me are the Ropeburn fight, which is literally one click, and shimmying on a ledge in level 2 of Mirror's Edge. The timing on said click in the first one just isn't in line with what I expect from the animation, so it took me ages to pull it off reliably. I've always been able to do the second one fairly reliably, but that remaining 5% of the time when the animation doesn't click and you fall off a ledge wastes enough time to kill a run.

More recently, the Anubis enemies in Persona 5. They have multiple insta-kill attacks and no weaknesses, and homonculi are much harder to get than in previous games. Unless you have something immune to light and dark, fighting one is basically a 10-20% chance of the game just saying "**** you" and sending you back to your last save.

And I also have to mention all of the combat in Prey. Like I said in the review thread, every encounter is a pointless war of attrition, to the point that it kills everything else about the game unless you cheat around it. It's a real shame, because what's hiding underneath that mess is brilliant.

Star Ocean: Till the End of Time is an okay game. Okay - it's good. Not the best. Still fun.

For the most part - good RPG. Nothing made me want to throw my controller at all. Then the most aggravating part was this dragon temple where you have four types of songs to play on a dragon flute. You need to play the dragon flute to get through these doors. You have a happy song, a playful song, a sad song and an angry song. If you play the wrong song at the door, you have to fight an enemy.

Now, each of the songs are played with a specific button press. I don't care to remember now becuase I hated this ****, but the most aggravating was the playful song. You had to press O lightly but a long press. I think it was the playful song. One of those.

GOD

FFFFFF

HRRRRNNNGGGG

I TRIED THREE DIFFERENT PLAYSTATION 2 CONTROLLERS THINKING THE BUTTON WAS OFF.

The worst was when I realized that I got confused between the playful song and the angry song. THE ANGRY SONG DOES NOT SOUND ANGRY WHAT THE ****

Maybe it was just because my tiny prepubescent brain couldn't handle collecting a few coins and ending the race in first place, but the only memories I have of those challenges are of anger and frustration.

But man, I've played DKR a few times through high school, college, and grad school, and I've gotta say that the Silver Coin Challenges are super well-designed. They double the amount of content in the game, and they're placed extremely well so as to still be possible while remaining a true challenge. They also make speedruns of that game supremely entertaining.

The vampire in Eternal Darkness.
It's not enough that the first half of the encounter is essentially a timed mission (at least it is if you want the Elephant Gun* & don't want 2 more enemies to fight), but you can't even save after the timed part--which is a real bugger, because the second half of the encounter is a painful boss fight against a strong, fast-attacking teleporter with one of the lower-healthed characters in the game.
Even with Shield up you flinch whenever he hits you, so have fun trying to cast Magick Attack or Damage Field.** That Shield won't last too long either; see the aforementioned "strong".

*And YOU DO WANT THE ELEPHANT GUN.
**And YOU DO WANT TO CAST DAMAGE FIELD.

The Blue Coins from Super Mario Sunshine. There are 240 of them in the game, amounting to 24 of the game's 120 Shines. They're spread out all over the place, many are either extremely well-hidden or acquired through completely unintuitive means (such as spraying a particular windmill or tree), some can only be found within a single episode of a level, and there's absolutely no indicator of which blue coins you've already gotten or even how many you've found in any given level (so if at the end of the game you find you're still missing a few and can't remember where you've already been, tough luck).

Many a time have I considered doing a 120 Shine run of this game, only to think "Oh yeah, the blue coins..."

^After one particularly trying year (I think the longest marathon they ever did), Mario Marathon restructured their level-unlock checklist specifically to ensure that the Sunshine blue-coin stars would always be last, thus greatly reducing the chances of having to do the blind hunting. A couple more years & a couple more new Mario games later, the blue coin stars were completely dropped from the level-unlock checklist.

^^ the only people I know who have bothered 120-shining that game are speedrunners because the coins are routed in so they already know which ones to get at every point in the run. And if they **** up they only lose like 3 hours of their lives rather than, say, 3 months.